CN1106881C - 催化剂的制备方法 - Google Patents

催化剂的制备方法 Download PDF

Info

Publication number: CN1106881C
Authority: CN; China
Prior art keywords: alkyl; unsubstituted; alkoxyl; aryl; general formula
Prior art date: 1996-11-01
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CN97121263A

Other languages

English (en)

Chinese (zh)

Other versions

CN1184003A (zh

Inventor

P·A·万德沙夫

R·科利

A·哈夫纳

A·胡尔巴克

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

Original Assignee

Ciba Geigy AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1996-11-01

Filing date

1997-10-31

Publication date

2003-04-30

1997-10-31 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1998-06-10 Publication of CN1184003A publication Critical patent/CN1184003A/zh

2003-04-30 Application granted granted Critical

2003-04-30 Publication of CN1106881C publication Critical patent/CN1106881C/zh

2017-10-31 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 24
238000002360 preparation method Methods 0.000 title abstract description 20
239000003054 catalyst Substances 0.000 title description 10
XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract description 39
229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 20
239000002253 acid Substances 0.000 claims abstract description 10
150000001345 alkine derivatives Chemical class 0.000 claims abstract description 9
ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 claims abstract description 9
VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical group PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 claims abstract description 8
150000003509 tertiary alcohols Chemical class 0.000 claims abstract description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
150000001875 compounds Chemical class 0.000 claims description 21
229910052736 halogen Inorganic materials 0.000 claims description 19
150000002367 halogens Chemical group 0.000 claims description 18
229910052757 nitrogen Inorganic materials 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 16
229910052799 carbon Inorganic materials 0.000 claims description 16
125000003545 alkoxy group Chemical group 0.000 claims description 15
229910052707 ruthenium Inorganic materials 0.000 claims description 15
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 14
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 13
125000003118 aryl group Chemical group 0.000 claims description 13
229910052760 oxygen Inorganic materials 0.000 claims description 13
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
125000000753 cycloalkyl group Chemical group 0.000 claims description 12
239000001301 oxygen Substances 0.000 claims description 12
150000008301 phosphite esters Chemical group 0.000 claims description 12
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
239000005864 Sulphur Substances 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
239000003513 alkali Substances 0.000 claims description 9
125000001072 heteroaryl group Chemical group 0.000 claims description 9
125000003710 aryl alkyl group Chemical group 0.000 claims description 8
150000002431 hydrogen Chemical class 0.000 claims description 8
229910052762 osmium Inorganic materials 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 7
125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
125000001118 alkylidene group Chemical group 0.000 claims description 6
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
229910014265 BrCl Inorganic materials 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 claims description 5
125000001624 naphthyl group Chemical group 0.000 claims description 5
SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 5
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 5
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
239000002585 base Substances 0.000 claims description 4
239000003446 ligand Substances 0.000 claims description 3
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 3
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 2
101150065749 Churc1 gene Proteins 0.000 claims description 2
102100038239 Protein Churchill Human genes 0.000 claims description 2
230000007935 neutral effect Effects 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
150000001721 carbon Chemical group 0.000 claims 1
XURVRZSODRHRNK-UHFFFAOYSA-N o-quinodimethane Chemical compound C=C1C=CC=CC1=C XURVRZSODRHRNK-UHFFFAOYSA-N 0.000 claims 1
229910052751 metal Inorganic materials 0.000 abstract description 5
239000002184 metal Substances 0.000 abstract description 5
150000001336 alkenes Chemical class 0.000 abstract description 4
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 abstract description 2
150000003839 salts Chemical class 0.000 abstract description 2
150000003333 secondary alcohols Chemical class 0.000 abstract description 2
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical group OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract 1
239000000460 chlorine Substances 0.000 description 53
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
-1 cyclic olefin Chemical class 0.000 description 47
239000000725 suspension Substances 0.000 description 43
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 40
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
238000003756 stirring Methods 0.000 description 24
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
125000004432 carbon atom Chemical group C* 0.000 description 14
VYXHVRARDIDEHS-QGTKBVGQSA-N (1z,5z)-cycloocta-1,5-diene Chemical compound C\1C\C=C/CC\C=C/1 VYXHVRARDIDEHS-QGTKBVGQSA-N 0.000 description 12
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 12
239000000047 product Substances 0.000 description 11
IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 description 11
239000012141 concentrate Substances 0.000 description 9
239000012954 diazonium Substances 0.000 description 8
239000000843 powder Substances 0.000 description 8
235000008708 Morus alba Nutrition 0.000 description 7
240000000249 Morus alba Species 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 6
229910052801 chlorine Inorganic materials 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
229910052731 fluorine Inorganic materials 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
150000001925 cycloalkenes Chemical class 0.000 description 4
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 4
150000001993 dienes Chemical class 0.000 description 4
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
230000002349 favourable effect Effects 0.000 description 4
239000012188 paraffin wax Substances 0.000 description 4
238000001556 precipitation Methods 0.000 description 4
238000001291 vacuum drying Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
125000004980 cyclopropylene group Chemical group 0.000 description 3
125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
125000005842 heteroatom Chemical group 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
125000002524 organometallic group Chemical group 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000012258 stirred mixture Substances 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical group CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
IBXNCJKFFQIKKY-UHFFFAOYSA-N 1-pentyne Chemical compound CCCC#C IBXNCJKFFQIKKY-UHFFFAOYSA-N 0.000 description 2
QEDJMOONZLUIMC-UHFFFAOYSA-N 1-tert-butyl-4-ethenylbenzene Chemical compound CC(C)(C)C1=CC=C(C=C)C=C1 QEDJMOONZLUIMC-UHFFFAOYSA-N 0.000 description 2
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
HECLRDQVFMWTQS-UHFFFAOYSA-N Dicyclopentadiene Chemical compound C1C2C3CC=CC3C1C=C2 HECLRDQVFMWTQS-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 2
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
238000013019 agitation Methods 0.000 description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 2
MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 2
239000004913 cyclooctene Substances 0.000 description 2
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
238000001035 drying Methods 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
239000007789 gas Substances 0.000 description 2
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
150000002527 isonitriles Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
UMIPWJGWASORKV-UHFFFAOYSA-N oct-1-yne Chemical compound CCCCCCC#C UMIPWJGWASORKV-UHFFFAOYSA-N 0.000 description 2
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
150000003512 tertiary amines Chemical group 0.000 description 2
125000001544 thienyl group Chemical group 0.000 description 2
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
OGQVROWWFUXRST-FNORWQNLSA-N (3e)-hepta-1,3-diene Chemical class CCC\C=C\C=C OGQVROWWFUXRST-FNORWQNLSA-N 0.000 description 1
CLNYHERYALISIR-FNORWQNLSA-N (3e)-nona-1,3-diene Chemical class CCCCC\C=C\C=C CLNYHERYALISIR-FNORWQNLSA-N 0.000 description 1
AFVDZBIIBXWASR-AATRIKPKSA-N (E)-1,3,5-hexatriene Chemical compound C=C\C=C\C=C AFVDZBIIBXWASR-AATRIKPKSA-N 0.000 description 1
PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical class C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
AMSMVCOBCOZLEE-UHFFFAOYSA-N 1,3,5-Norcaratriene Chemical compound C1=CC=C2CC2=C1 AMSMVCOBCOZLEE-UHFFFAOYSA-N 0.000 description 1
QTYUSOHYEPOHLV-FNORWQNLSA-N 1,3-Octadiene Chemical class CCCC\C=C\C=C QTYUSOHYEPOHLV-FNORWQNLSA-N 0.000 description 1
GWYPDXLJACEENP-UHFFFAOYSA-N 1,3-cycloheptadiene Chemical compound C1CC=CC=CC1 GWYPDXLJACEENP-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical group CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical class CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical group NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
HLQMBZMIEPDGLN-UHFFFAOYSA-N C1C=[Ru]1 Chemical compound C1C=[Ru]1 HLQMBZMIEPDGLN-UHFFFAOYSA-N 0.000 description 1
241000282461 Canis lupus Species 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
CGMDPTNRMYIZTM-UHFFFAOYSA-N Sarohornene Natural products CC=CC=CC=CC CGMDPTNRMYIZTM-UHFFFAOYSA-N 0.000 description 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
KDUIUFJBNGTBMD-VXMYFEMYSA-N cyclooctatetraene Chemical compound C1=C\C=C/C=C\C=C1 KDUIUFJBNGTBMD-VXMYFEMYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
239000002360 explosive Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
150000002240 furans Chemical class 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000004519 grease Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
USKZHEQYENVSMH-UHFFFAOYSA-N hepta-1,3,5-triene Chemical compound CC=CC=CC=C USKZHEQYENVSMH-UHFFFAOYSA-N 0.000 description 1
AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical class CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000002460 imidazoles Chemical class 0.000 description 1
150000002475 indoles Chemical class 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 1
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
150000002908 osmium compounds Chemical class 0.000 description 1
RFPMGSKVEAUNMZ-UHFFFAOYSA-N pentylidene Chemical group [CH2+]CCC[CH-] RFPMGSKVEAUNMZ-UHFFFAOYSA-N 0.000 description 1
229930015698 phenylpropene Natural products 0.000 description 1
125000004437 phosphorous atom Chemical group 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
230000007096 poisonous effect Effects 0.000 description 1
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
150000003217 pyrazoles Chemical class 0.000 description 1
150000003233 pyrroles Chemical class 0.000 description 1
150000003235 pyrrolidines Chemical class 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 description 1
NNLBRYQGMOYARS-UHFFFAOYSA-N thiane 1-oxide Chemical compound O=S1CCCCC1 NNLBRYQGMOYARS-UHFFFAOYSA-N 0.000 description 1
GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
VAVZSHDIGAQVIE-UHFFFAOYSA-N toluene;tricyclohexylphosphane Chemical compound CC1=CC=CC=C1.C1CCCCC1P(C1CCCCC1)C1CCCCC1 VAVZSHDIGAQVIE-UHFFFAOYSA-N 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
125000006493 trifluoromethyl benzyl group Chemical group 0.000 description 1
YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F19/00—Metal compounds according to more than one of main groups C07F1/00 - C07F17/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0046—Ruthenium compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/002—Osmium compounds
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/72—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from metals not provided for in group C08F4/44
- C08F4/80—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from metals not provided for in group C08F4/44 selected from iron group metals or platinum group metals

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)

CN97121263A 1996-11-01 1997-10-31 催化剂的制备方法 Expired - Fee Related CN1106881C (zh)

Applications Claiming Priority (3)

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CH270796		1996-11-01
CH2707/1996		1996-11-01
CH2707/96		1996-11-01

Publications (2)

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CN1184003A CN1184003A (zh)	1998-06-10
CN1106881C true CN1106881C (zh)	2003-04-30

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US (1)	US5912376A (de)
EP (1)	EP0839821B1 (de)
JP (1)	JP3932467B2 (de)
KR (1)	KR100525181B1 (de)
CN (1)	CN1106881C (de)
AT (1)	ATE228140T1 (de)
AU (1)	AU735786B2 (de)
BR (1)	BR9705398A (de)
CA (1)	CA2219942C (de)
DE (1)	DE59708768D1 (de)
TW (1)	TW344677B (de)

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US6159890A (en) *	1996-04-30	2000-12-12	Bp Amoco Corporation	Ruthenium-containing catalyst system for olefin metathesis
US6156692A (en) *	1996-04-30	2000-12-05	Bp Amoco Corporation	Ruthenium-containing catalyst composition for olefin metathesis
EP0844264B1 (de) *	1996-11-15	2003-01-08	Ciba SC Holding AG	Katalysatorgemisch für ringöffnende Metathesepolymerisation
DE69818240T2 (de) *	1997-03-06	2004-07-01	Ciba Speciality Chemicals Holding Inc.	Neue katalysatoren
US6175047B1 (en) *	1997-12-26	2001-01-16	Takasago International Corporation	Ruthenium metathesis catalyst and method for producing olefin reaction product by metathesis reaction using the same
DE19854869A1 (de) *	1998-11-27	2000-05-31	Basf Ag	Verfahren zur Herstellung von Rutheniumkomplexen
CA2441821A1 (en) *	2001-04-16	2002-10-24	Yeda Research And Development Co. Ltd.	New method for the preparation of metal carbene complexes
US8592336B2 (en)	2006-04-11	2013-11-26	Agency For Science, Technology And Research	Catalysts for ring-closing metathesis
EP2010318B1 (de)	2006-04-11	2014-04-02	Agency for Science, Technology and Research	Katalysatoren für ringschlussmetathese
JP5206068B2 (ja) *	2008-03-28	2013-06-12	日本ゼオン株式会社	ルテニウム錯体化合物の製造方法
WO2009124977A1 (de)	2008-04-08	2009-10-15	Evonik Degussa Gmbh	Verfahren zur herstellung von ruthenium-carben-komplexen
GB201004732D0 (en)	2010-03-22	2010-05-05	Univ Aberdeen	Ruthenium complexes for use in olefin metathesis
WO2012076426A1 (de)	2010-12-08	2012-06-14	Basf Se	Verfahren zur herstellung einer wässrigen polymerisatdispersion
EP3081572A1 (de) *	2015-04-16	2016-10-19	ARLANXEO Deutschland GmbH	Ruthenium- oder osmium-basierte komplexe katalysatoren
US11065609B2 (en) *	2016-08-24	2021-07-20	Umicore Ag & Co. Kg	Synthesis and characterization of metathesis catalysts
KR102702569B1 (ko)	2017-12-08	2024-09-06	아란세오 도이치란드 게엠베하	루테늄 착물 촉매를 사용하여 니트릴 고무를 생성하기 위한 방법

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CN1198752A (zh) *	1995-08-03	1998-11-11	加州理工学院	高置换活性的钌和锇金属卡宾络合物

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1997
- 1997-10-22 EP EP97810786A patent/EP0839821B1/de not_active Expired - Lifetime
- 1997-10-22 AT AT97810786T patent/ATE228140T1/de not_active IP Right Cessation
- 1997-10-22 DE DE59708768T patent/DE59708768D1/de not_active Expired - Lifetime
- 1997-10-24 AU AU42873/97A patent/AU735786B2/en not_active Ceased
- 1997-10-27 US US08/958,680 patent/US5912376A/en not_active Expired - Lifetime
- 1997-10-27 KR KR1019970055157A patent/KR100525181B1/ko not_active Expired - Fee Related
- 1997-10-30 TW TW086116149A patent/TW344677B/zh active
- 1997-10-30 CA CA002219942A patent/CA2219942C/en not_active Expired - Fee Related
- 1997-10-30 JP JP31447797A patent/JP3932467B2/ja not_active Expired - Fee Related
- 1997-10-31 CN CN97121263A patent/CN1106881C/zh not_active Expired - Fee Related
- 1997-11-03 BR BR9705398A patent/BR9705398A/pt not_active IP Right Cessation

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CN1198752A (zh) *	1995-08-03	1998-11-11	加州理工学院	高置换活性的钌和锇金属卡宾络合物

Also Published As

Publication number	Publication date
CA2219942A1 (en)	1998-05-01
AU735786B2 (en)	2001-07-12
EP0839821B1 (de)	2002-11-20
KR100525181B1 (ko)	2006-01-12
EP0839821A2 (de)	1998-05-06
TW344677B (en)	1998-11-11
CN1184003A (zh)	1998-06-10
JPH10180114A (ja)	1998-07-07
EP0839821A3 (de)	2000-01-05
CA2219942C (en)	2006-11-21
JP3932467B2 (ja)	2007-06-20
ATE228140T1 (de)	2002-12-15
MX9708388A (es)	1998-05-31
KR19980041960A (ko)	1998-08-17
BR9705398A (pt)	1999-05-04
US5912376A (en)	1999-06-15
DE59708768D1 (de)	2003-01-02
AU4287397A (en)	1998-05-07

Legal Events

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1998-06-10	C06	Publication
1998-06-10	PB01	Publication
2000-01-05	C10	Entry into substantive examination
2000-01-05	SE01	Entry into force of request for substantive examination
2003-04-30	C14	Grant of patent or utility model
2003-04-30	GR01	Patent grant
2016-12-21	CF01	Termination of patent right due to non-payment of annual fee	Granted publication date: 20030430 Termination date: 20151031
2016-12-21	EXPY	Termination of patent right or utility model

Publication	Publication Date	Title
CN1106881C (zh)	2003-04-30	催化剂的制备方法
EP2350105B1 (de)	2013-12-25	Verfahren zur herstellung von ruthenium-indenyliden-carben-katalysatoren
JP4531253B2 (ja)	2010-08-25	Ｎ−複素環式カルベン配位子を含むルテニウムのアルキリデン錯体；オレフィンメタセシス用の高活性選択性触媒としての使用
CN1134448C (zh)	2004-01-14	钌或锇复分解催化剂的合成
Opstal et al.	2003	Easily accessible and robust olefin-metathesis catalysts based on ruthenium vinylidene complexes
CA2361148C (en)	2009-06-30	Novel methods for cross-metathesis of terminal olefins
US5146033A (en)	1992-09-08	Homogeneous rhenium catalysts for metathesis of olefins
US8846938B2 (en)	2014-09-30	Method for preparation of ruthenium-based metathesis catalysts with chelating alkylidene ligands
Farrell et al.	2020	Decomposition of vanadium (V) alkylidenes relevant to olefin metathesis
CA2302652A1 (en)	2000-10-02	Ruthenium or osmium catalysts for olefin metathesis reactions
Schädle et al.	2015	Rare-earth metal methylidene complexes with Ln 3 (μ 3-CH 2)(μ 3-Me)(μ 2-Me) 3 core structure
US5087710A (en)	1992-02-11	Homogeneous rhenium catalysts for metathesis of olefins
EP1604964B1 (de)	2009-06-10	Nullwertiger übergangsmetallkomplex und verfahren zur synthese metallorganischer verbindungen unter verwendung deskomplexes als ausgangsmaterial
EP1950216B1 (de)	2018-08-29	Verfahren zur herstellung einer organischen übergangsmetallkomplexverbindung
FR2726563A1 (fr)	1996-05-10	Nouveaux composes du rhenium et de l'aluminium, leur preparation et leur utilisation en tant que catalyseurs
Siano et al.	2011	Activity and stereoselectivity of Ru-based catalyst bearing a fluorinated imidazolinium ligand
WO2019180230A1 (en)	2019-09-26	Tetraphenylphenoxy tungsten oxo alkylidene complexes, methods of making same and use thereof
JP4131074B2 (ja)	2008-08-13	ルテニウム化合物の製造方法
Auzias et al.	2009	New Dinuclear Ru2 (CO) 4 Sawhorse‐Type Complexes Containing Bridging Carboxylato Ligands
Guidone et al.	2015	Ruthenium indenylidene “1st generation” olefin metathesis catalysts containing triisopropyl phosphite
Tamm et al.	2003	Molybdenum alkylidene complexes with linked cycloheptatrienyl–phosphane ligands for potential use in olefin metathesis
KR20010023107A (ko)	2001-03-26	루테늄 착물의 제조방법
Ohashi et al.	2006	Hexapalladium cluster: Unique cluster construction reaction of cyclic Pd3 (CNC6H3Me2-2, 6) 6 and linear [Pd3 (CNC6H3Me2-2, 6) 8] 2+
KR20050083870A (ko)	2005-08-26	팔라듐(0)을 함유한 화합물들의 생산 방법
Barinova et al.	2010	Carbene complexes of molybdenum and tungsten Et3E-CH= M (NAr)(OR) 2 (M= Mo, W; E= Si, Ge) and π-complex of molybdenum (RO) 2 (ArN) Mo (CH2= CH-GeEt3). Synthesis and catalytic properties